Hellooooooo,

Happy Valentine’s Day 10Xers (should I start calling you guys that?... umm.. Why not!)

You guys are the one true love of my life, supporting me through EVERYTHINGGG.

Side note: Is it okay for 1 person to have 787 valentines?

This week, I had two inquiries about newsletter writing.

One founder call.
One “what’s your setup and retainer cost?” message.

And someone suggested I start a newsletter cohort.

That’s 5 newsletter-related nudges this year. (and it’s only mid- Feb)

I mentioned this on LinkedIn and got a bunch of questions:

What strategy do you follow?
Where does someone learn this?
How does monetization work?
Do you use AI?
Is there a specific format?

So let’s look at it properly.

Newsletter strategy starts with one uncomfortable question: what is this email supposed to do for the business?

For example, if you’re a B2B consultant, the newsletter might exist to warm up decision-makers so that when they need your service, you are the obvious choice. In that case, your emails would share thinking, frameworks, client scenarios, maybe even mistakes you’ve seen across companies.

If you’re a SaaS founder, the newsletter might exist to educate your ICP about a problem your product solves. So instead of random industry news, you send breakdowns that lead the reader toward understanding why your solution makes sense.

If you’re building a personal brand, the newsletter might be positioning. Opinion-led, perspective-heavy, designed to make people think, “I like how this person thinks.”

Different objective. Different content.

Without this clarity, newsletters become weekly essays with no direction.

You don’t start with a course. You start with your own inbox.

Look at a newsletter you actually read fully. Why do you open it? Is it because the subject lines are specific? Because the writer has a strong point of view? Because it feels like a conversation, not a lecture?

For example, some newsletters open with a sharp personal story (like this one) and then extract a business lesson. Others open with a bold claim and then back it up with data or experience. That opening pattern is a strategy.

Then send your own.

You’ll learn more from writing 10 issues and watching how people respond than from consuming 50 threads about “email marketing secrets.”

Most people think monetization equals ads.

It can. But that’s not where I start.

If a founder already closes high-ticket consulting deals, the newsletter can drive discovery calls. That’s monetization.

If a creator sells a course twice a year, the newsletter nurtures the audience until launch week. That’s monetization.

If a SaaS company has a free trial, the newsletter can push case studies and use cases that move readers into the product. That’s monetization.

Ads and sponsorships come later, when the audience is consistent and valuable.

Revenue should feel like a natural extension of the thinking you’re already sharing.

Yes, I use AI. But not as a ghostwriter.

If I’m writing four newsletters a month for a client, I’ll use AI to generate angle options. For example, I might input a client’s recent webinar and ask for five potential newsletter hooks from different perspectives.

I’ll use it to test subject line variations.
I’ll use it to tighten transitions.
I’ll use it to repurpose one newsletter into three LinkedIn posts.

But the core idea, the positioning, the voice, the final edit, that’s human work.

AI accelerates the process. It doesn’t replace judgment.

There isn’t a magical template, but there is flow.

A strong opening that earns attention.
A clear insight or argument.
An example, story, or breakdown that proves the point.
One focused CTA.

For instance, if the insight is about why most startups fail at onboarding, the CTA could be, “Reply with your onboarding flow and I’ll share one improvement idea.” That creates conversation. That creates leads.

Just one action. Not five.

That’s it for today! Let me know if you have other questions, and I’ll be happy to answer. Also, reply to this email if I missed previous replies. I have been on and off work, so I might have missed it.

Now tell me honestly, should we do that newsletter cohort?

-Nikita